Lithium hydroxide, monohydrate → HCID 58386308, compound

HRID 64035Notes

Reaction equation

HRID 64035 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24](=[O:29])[C:25]([O:27]C)=[O:26])=[C:16]2[N:15]=1.O[Li].O>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([NH:23][C:24](=[O:29])[C:25]([OH:27])=[O:26])=[C:16]2[N:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58386261HCID 58386261, compound

Product 1

HCID 58386308HCID 58386308, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

(R)-methyl 2-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-ylamino)-2-oxoacetate (Example 104; 100 mg, 0.249 mmol) was dissolved in a mixture solvent of THF:MeOH:water (2:2:1, 1 mL), followed by addition of LiOH—H2O (31.4 mg, 0.747 mmol). The reaction was stirred at ambient temperature for 10 minutes to reach completion. The reaction was concentrated, re-dissolved in water (20 mL) and acidified with 6 N HCl. The precipitate was vacuum-filtered, rinsed with water, heptane, and dried on high vacuum, giving the final product as a fine pale-yellowish powder (50 mg, 52% yield). MS (apci negative) m/z=386.1 (M−H).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionre-dissolved in water (20 mL)
  3. filtrationThe precipitate was vacuum-filtered
  4. washrinsed with water, heptane
  5. customdried on high vacuum

Sources & evidence

ORD record
ord-a38f828020a84e71b7915a5f32935a8c
Source dataset
uspto-grants-2016_09
Patent number
US09447104B2

Reaction notes

Loading…